JPH04234859A - アズラクトンマイケル付加物 - Google Patents

アズラクトンマイケル付加物

Info

Publication number: JPH04234859A
Authority: JP; Japan
Prior art keywords: independently; formula; michael; group; azlactone
Prior art date: 1990-03-28
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP3063428A

Other languages

English (en)

Japanese (ja)

Inventor

Dean M Moren

ディーン　マイケル　モレン

Steven M Heilmann

スティーブン　マイケル　ヘイルマン

Larry R Krepski

ラリー　リチャード　クリプスキ

Jerald K Rasmussen

ジェラルド　ケネス　ラスミュッセン

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

3M Co

Original Assignee

Minnesota Mining and Manufacturing Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-03-28

Filing date

1991-03-27

Publication date

1992-08-24

1991-03-27 Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co

1992-08-24 Publication of JPH04234859A publication Critical patent/JPH04234859A/ja

Status Pending legal-status Critical Current

Links

IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical compound O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 title claims abstract description 25
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 28
229910052799 carbon Inorganic materials 0.000 claims abstract description 25
239000003054 catalyst Substances 0.000 claims abstract description 21
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
125000003118 aryl group Chemical group 0.000 claims abstract description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
239000000126 substance Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
238000000034 method Methods 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000006413 ring segment Chemical group 0.000 claims description 7
125000002947 alkylene group Chemical group 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000004450 alkenylene group Chemical group 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000002993 cycloalkylene group Chemical group 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
125000000732 arylene group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000005647 linker group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 19
150000001875 compounds Chemical class 0.000 abstract description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 16
239000002253 acid Substances 0.000 abstract description 15
239000000178 monomer Substances 0.000 abstract description 10
238000000576 coating method Methods 0.000 abstract description 8
150000002081 enamines Chemical class 0.000 abstract description 7
239000000853 adhesive Substances 0.000 abstract description 5
230000001070 adhesive effect Effects 0.000 abstract description 5
229910052698 phosphorus Inorganic materials 0.000 abstract description 5
239000000565 sealant Substances 0.000 abstract description 4
239000011248 coating agent Substances 0.000 abstract description 2
-1 poly(isocyanate) Polymers 0.000 description 28
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
238000006957 Michael reaction Methods 0.000 description 20
239000012038 nucleophile Substances 0.000 description 17
QKPKBBFSFQAMIY-UHFFFAOYSA-N 2-ethenyl-4,4-dimethyl-1,3-oxazol-5-one Chemical group CC1(C)N=C(C=C)OC1=O QKPKBBFSFQAMIY-UHFFFAOYSA-N 0.000 description 15
239000012948 isocyanate Substances 0.000 description 15
229920000642 polymer Polymers 0.000 description 15
150000002513 isocyanates Chemical class 0.000 description 14
239000000047 product Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
239000000370 acceptor Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
150000001412 amines Chemical class 0.000 description 10
238000010438 heat treatment Methods 0.000 description 10
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
238000005160 1H NMR spectroscopy Methods 0.000 description 8
150000001721 carbon Chemical group 0.000 description 8
239000000463 material Substances 0.000 description 8
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
125000000524 functional group Chemical group 0.000 description 7
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
239000000376 reactant Substances 0.000 description 7
238000006845 Michael addition reaction Methods 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 6
125000004429 atom Chemical group 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000004593 Epoxy Substances 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
238000007792 addition Methods 0.000 description 4
230000008901 benefit Effects 0.000 description 4
125000005842 heteroatom Chemical group 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000004806 packaging method and process Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000004132 cross linking Methods 0.000 description 3
150000002085 enols Chemical group 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229920001002 functional polymer Polymers 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000000269 nucleophilic effect Effects 0.000 description 3
150000003018 phosphorus compounds Chemical class 0.000 description 3
229920000768 polyamine Polymers 0.000 description 3
229920005862 polyol Polymers 0.000 description 3
150000003077 polyols Chemical class 0.000 description 3
238000007142 ring opening reaction Methods 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
229910052710 silicon Inorganic materials 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
DANDTMGGYNCQLG-UHFFFAOYSA-N 4h-1,3-oxazol-5-one Chemical class O=C1CN=CO1 DANDTMGGYNCQLG-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
YNDUPGQMECPWKD-UHFFFAOYSA-N [O-][N+](=O)S[N+]([O-])=O Chemical compound [O-][N+](=O)S[N+]([O-])=O YNDUPGQMECPWKD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical group O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 2
SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000010276 construction Methods 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
239000003431 cross linking reagent Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
239000012990 dithiocarbamate Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000006575 electron-withdrawing group Chemical group 0.000 description 2
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000008204 material by function Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
238000005935 nucleophilic addition reaction Methods 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
229910000073 phosphorus hydride Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
125000001453 quaternary ammonium group Chemical group 0.000 description 2
102220007331 rs111033633 Human genes 0.000 description 2
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 2
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
239000002002 slurry Substances 0.000 description 2
150000003384 small molecules Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
238000007155 step growth polymerization reaction Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
229960002317 succinimide Drugs 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
150000007970 thio esters Chemical class 0.000 description 2
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
KOFSFYBXUYHNJL-UHFFFAOYSA-N 1-(cyclopenten-1-yl)pyrrolidine Chemical compound C1CCCN1C1=CCCC1 KOFSFYBXUYHNJL-UHFFFAOYSA-N 0.000 description 1
GGZHVNZHFYCSEV-UHFFFAOYSA-N 1-Phenyl-5-mercaptotetrazole Chemical compound SC1=NN=NN1C1=CC=CC=C1 GGZHVNZHFYCSEV-UHFFFAOYSA-N 0.000 description 1
VXUVJQIYKFXQMR-UHFFFAOYSA-N 2-ethenyl-4,4-dimethyl-5h-1,3-oxazin-6-one Chemical compound CC1(C)CC(=O)OC(C=C)=N1 VXUVJQIYKFXQMR-UHFFFAOYSA-N 0.000 description 1
DMDNNZDDQOLFPX-UHFFFAOYSA-N 2-ethenyl-4-ethyl-4-methyl-1,3-oxazol-5-one Chemical compound CCC1(C)N=C(C=C)OC1=O DMDNNZDDQOLFPX-UHFFFAOYSA-N 0.000 description 1
CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical group O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
MUWZQYSJSCDUDT-UHFFFAOYSA-N 4,4-dimethyl-2-prop-1-en-2-yl-1,3-oxazol-5-one Chemical compound CC(=C)C1=NC(C)(C)C(=O)O1 MUWZQYSJSCDUDT-UHFFFAOYSA-N 0.000 description 1
WAUGGKDVKLYWET-UHFFFAOYSA-N 4,5-dihydrooxazin-6-one Chemical group O=C1CCC=NO1 WAUGGKDVKLYWET-UHFFFAOYSA-N 0.000 description 1
101100439662 Arabidopsis thaliana CHR5 gene Proteins 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229920008347 Cellulose acetate propionate Polymers 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
229920002396 Polyurea Polymers 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229920003232 aliphatic polyester Polymers 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000004984 aromatic diamines Chemical class 0.000 description 1
229940125717 barbiturate Drugs 0.000 description 1
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
230000000711 cancerogenic effect Effects 0.000 description 1
150000001715 carbamic acids Chemical class 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
231100000315 carcinogenic Toxicity 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000006210 cyclodehydration reaction Methods 0.000 description 1
230000002950 deficient Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
125000005594 diketone group Chemical group 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000000539 dimer Substances 0.000 description 1
BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
239000012834 electrophilic reactant Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
RJLZSKYNYLYCNY-UHFFFAOYSA-N ethyl carbamate;isocyanic acid Chemical compound N=C=O.CCOC(N)=O RJLZSKYNYLYCNY-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
230000036541 health Effects 0.000 description 1
230000005802 health problem Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
150000002829 nitrogen Chemical class 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000008520 organization Effects 0.000 description 1
239000000123 paper Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920006149 polyester-amide block copolymer Polymers 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920006254 polymer film Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000000985 reactive dye Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229920006114 semi-crystalline semi-aromatic polyamide Polymers 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000003860 storage Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
239000013638 trimer Substances 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/36—One oxygen atom
- C07D263/42—One oxygen atom attached in position 5

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Polyesters Or Polycarbonates (AREA)
Plural Heterocyclic Compounds (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Polyurethanes Or Polyureas (AREA)
Paints Or Removers (AREA)
Adhesives Or Adhesive Processes (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP3063428A 1990-03-28 1991-03-27 アズラクトンマイケル付加物 Pending JPH04234859A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US500768		1990-03-28
US07/500,768 US5149806A (en)	1990-03-28	1990-03-28	Azlactone michael adducts

Publications (1)

Publication Number	Publication Date
JPH04234859A true JPH04234859A (ja)	1992-08-24

Family

ID=23990854

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3063428A Pending JPH04234859A (ja)	1990-03-28	1991-03-27	アズラクトンマイケル付加物

Country Status (6)

Country	Link
US (1)	US5149806A (fr)
EP (1)	EP0449488B1 (fr)
JP (1)	JPH04234859A (fr)
KR (1)	KR0163787B1 (fr)
DE (1)	DE69130431T2 (fr)
ES (1)	ES2122967T3 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2004018859A (ja) *	2002-06-14	2004-01-22	Dainippon Ink & Chem Inc	硬化性組成物

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5268473A (en) *	1990-03-28	1993-12-07	Minnesota Mining And Manufacturing Company	Azlactone Michael adducts
AU642284B2 (en) *	1990-08-31	1993-10-14	Minnesota Mining And Manufacturing Company	Post-processing stabilization of photothermographic emulsions
US5837751A (en) *	1990-11-28	1998-11-17	Loctite Corporation	Norbornenyl azlactones
JPH04288059A (ja) *	1991-03-14	1992-10-13	Nippon Paint Co Ltd	複素環化合物及びその製造法
FR2690918B1 (fr) *	1992-05-06	2001-12-28	Poudres & Explosifs Ste Nale	Utilisation d'un arylsulfonyluréthanne comme résine garnissante dans les vernis à ongles nitrocellulosiques. Nouveaux arylsulfonyluréthannes et nouveaux vernis à ongles nitrocellulosiques.
US5292514A (en) *	1992-06-24	1994-03-08	Minnesota Mining And Manufacturing Company	Azlactone-functional substrates, corneal prostheses, and manufacture and use thereof
US5705585A (en)	1993-06-30	1998-01-06	Arqule, Inc.	Aminimide-containing molecules and materials as molecular recognition agents
KR950702216A (ko) *	1992-06-30	1995-06-19	조셉 씨, 호간	옥사졸론 유도물질(oxazlone derived materials)
US5362812A (en) *	1993-04-23	1994-11-08	Minnesota Mining And Manufacturing Company	Reactive polymeric dyes
US5408002A (en) *	1993-09-09	1995-04-18	Minnesota Mining And Manufacturing Company	Azlactone-functional polymer blends, articles produced therefrom and methods for preparing both
WO1995017903A1 (fr) *	1993-12-28	1995-07-06	Arqule Partners, L.P.	Structure et synthese modulaire de molecules derivees de l'oxazolone
US7034110B2 (en) *	1994-01-05	2006-04-25	Arqule, Inc.	Method of identifying chemical compounds having selected properties for a particular application
AU704878B2 (en)	1994-01-05	1999-05-06	Arqule, Inc.	Method of making polymers having specific properties
US5510421A (en) *	1994-05-26	1996-04-23	Minnesota Mining And Manufacturing Company	Azlactone-functional membranes and methods of preparing and using same
US5734082A (en)	1994-10-20	1998-03-31	Arqule Inc.	Hydroxyethyl aminimides
US5712171A (en)	1995-01-20	1998-01-27	Arqule, Inc.	Method of generating a plurality of chemical compounds in a spatially arranged array
WO1996031263A1 (fr)	1995-04-06	1996-10-10	Arqule, Inc.	Procede de purification, d'analyse et de caracterisation rapides de collections de composes chimiques
US5840106A (en) *	1995-11-13	1998-11-24	Minnesota Mining And Manufacturing Company	Water-based pigmented inks
US5714632A (en) *	1995-11-13	1998-02-03	Minnesota Mining And Manufacturing Company	Azlactone-based surfactants
US5962412A (en)	1996-06-10	1999-10-05	Arqule, Inc.	Method of making polymers having specific properties
US6376619B1 (en) *	1998-04-13	2002-04-23	3M Innovative Properties Company	High density, miniaturized arrays and methods of manufacturing same
US6630243B2 (en) *	1999-05-20	2003-10-07	Bausch & Lomb Incorporated	Surface treatment of silicone hydrogel contact lenses comprising hydrophilic polymer chains attached to an intermediate carbon coating
US6482638B1 (en) *	1999-12-09	2002-11-19	3M Innovative Properties Company	Heat-relaxable substrates and arrays
US6794458B2 (en) *	2001-05-18	2004-09-21	3M Innovative Properties Company	Azlactone-functional hydrophilic coatings and hydrogels
EP1581260B1 (fr) *	2002-12-31	2014-09-17	Nektar Therapeutics	Reactifs polymeres comprenant une cetone ou un groupe fonctionnel apparente
US7883720B2 (en)	2003-07-09	2011-02-08	Wisconsin Alumni Research Foundation	Charge-dynamic polymers and delivery of anionic compounds
US8012693B2 (en)	2003-12-16	2011-09-06	3M Innovative Properties Company	Analysis of chemically crosslinked cellular samples
US7556858B2 (en) *	2004-09-30	2009-07-07	3M Innovative Properties Company	Substrate with attached dendrimers
JP2008547005A (ja) *	2005-06-16	2008-12-25	スリーエムイノベイティブプロパティズカンパニー	マススペクトルを用いた化学的に架橋された細胞サンプルの分類方法
US8834918B2 (en) *	2007-01-22	2014-09-16	Wisconsin Alumni Research Foundation	Modified multilayered film
US7842762B2 (en)	2007-08-08	2010-11-30	Ppg Industries Ohio, Inc.	Electrodepositable coating composition containing a cyclic guanidine
US8071210B2 (en) *	2007-10-09	2011-12-06	Wiscousin Alumni Research Foundation	Covalent assembly of ultrathin polymeric films
US8563560B2 (en)	2011-02-25	2013-10-22	Ppg Industries Ohio, Inc.	Preparation of bicyclic guanidine salts in an aqueous media
US9068089B2 (en)	2013-03-15	2015-06-30	Ppg Industries Ohio, Inc.	Phenolic admix for electrodepositable coating composition containing a cyclic guanidine
US9688874B2 (en)	2013-10-25	2017-06-27	Ppg Industries Ohio, Inc.	Method of making a bicyclic guanidine-cured acrylic coating
CN106631861B (zh) *	2016-12-12	2018-11-30	骆惠红	一种医药中间体n,n′-二苯基丙二酰胺的合成工艺

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE447382A (fr) *	1941-11-11
DE1745348A1 (de) *	1967-12-01	1971-09-09	Roehm Gmbh	Azlactongruppen enthaltende Mischpolymerisate
GB1296705A (fr) *	1969-07-22	1972-11-15
DE2522192C2 (de) *	1975-05-17	1985-05-09	Deutsche Texaco Ag, 2000 Hamburg	Pulverfoermige ueberzugsmittel
US4291152A (en) *	1979-03-27	1981-09-22	Teijin Limited	Process for producing aromatic polyesters having increased degrees of polymerization
US4266040A (en) *	1980-06-27	1981-05-05	Desoto, Inc.	Polyazlactone-electron deficient ethylenically unsaturated resinous compositions and method for foaming same
US4485236A (en) *	1982-09-27	1984-11-27	Minnesota Mining And Manufacturing Company	Azlactone-functional compounds
US4667012A (en) *	1984-12-14	1987-05-19	Minnesota Mining And Manufacturing Company	Imidazolinone-containing polymer and copolymer
US4852969A (en) *	1988-03-17	1989-08-01	Minnesota Mining And Manufacturing Company	Silyl 2-amidoacetate and silyl 3-amidopropionate compositions and optical fiber made therefrom
US5157108A (en) *	1989-12-12	1992-10-20	Minnesota Mining And Manufacturing Company	Thermally sensitive linkages

1990
- 1990-03-28 US US07/500,768 patent/US5149806A/en not_active Expired - Lifetime
1991
- 1991-03-20 ES ES91302394T patent/ES2122967T3/es not_active Expired - Lifetime
- 1991-03-20 DE DE69130431T patent/DE69130431T2/de not_active Expired - Fee Related
- 1991-03-20 EP EP91302394A patent/EP0449488B1/fr not_active Expired - Lifetime
- 1991-03-27 JP JP3063428A patent/JPH04234859A/ja active Pending
- 1991-03-27 KR KR1019910004783A patent/KR0163787B1/ko not_active Expired - Fee Related

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2004018859A (ja) *	2002-06-14	2004-01-22	Dainippon Ink & Chem Inc	硬化性組成物

Also Published As

Publication number	Publication date
KR0163787B1 (ko)	1998-12-01
EP0449488B1 (fr)	1998-11-04
EP0449488A1 (fr)	1991-10-02
US5149806A (en)	1992-09-22
KR910016718A (ko)	1991-11-05
DE69130431D1 (de)	1998-12-10
ES2122967T3 (es)	1999-01-01
DE69130431T2 (de)	1999-05-27

Publication	Publication Date	Title
JPH04234859A (ja)	1992-08-24	アズラクトンマイケル付加物
US3567763A (en)	1971-03-02	Ester polyisocyanates
JP4490813B2 (ja)	2010-06-30	ウレトジオン基を含むイソシアネート
US5914383A (en)	1999-06-22	Isocyanate trimers containing iminooxadiazine dione groups, their preparation and use
JP4347945B2 (ja)	2009-10-21	Ｃｈ酸性エステルでブロックした熱黄変安定化ポリイソシアネート
JP5554307B2 (ja)	2014-07-23	修飾されたイソシアネート
JP4029047B2 (ja)	2008-01-09	ウレトジオン、イソシアヌレートおよびイミノオキサジアジンジオン構造を有する脂肪族ポリイソシアネートの製造方法
JPS6123807B2 (fr)	1986-06-07
EP3677616B1 (fr)	2022-07-20	Procédé de production de polyuréthanes sans isocyanate
US5268473A (en)	1993-12-07	Azlactone Michael adducts
JPH0261464B2 (fr)	1990-12-20
JPS58118575A (ja)	1983-07-14	新規なイソシアネ−ト−イソシアヌレ−トならびにその製造法
JPH032864B2 (fr)	1991-01-17
US5545705A (en)	1996-08-13	Aldimines based on 2-methyl-1,5-pentane diamine and their use for the production of polyurea coatings
US3968104A (en)	1976-07-06	Extremely low viscosity adducts of lactams with alcohols
US4293693A (en)	1981-10-06	Hemiacetals of adducts of acrolein and isocyanuric acid
US3939200A (en)	1976-02-17	Aliphatic acyl-containing amine hydrochlorides
US4321375A (en)	1982-03-23	Acetals of adducts of acrolein and isocyanuric acid
US4619999A (en)	1986-10-28	Aliphatic isocyanate compounds
US4375538A (en)	1983-03-01	Polymer compositions comprising adducts of acrolein and isocyanuric acid
EP0177059B1 (fr)	1991-01-16	Polyisocyanates modifiés ayant la structure du biuret et procédé de préparation
US3059023A (en)	1962-10-16	Process for the production of chlorine and bromine substituted carbamates
US3217003A (en)	1965-11-09	Method for preparing triaryl isocyanurates
EP0055092B1 (fr)	1985-04-17	Acétales de produits d'addition d'acroléine et d'acide isocyanurique et compositions de polymère les contenant
JPS62161780A (ja)	1987-07-17	新規なアゼチジンジオン化合物

JPH04234859A - アズラクトンマイケル付加物 - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=23990854

Family Applications (1)

Country Status (6)

Cited By (1)

Families Citing this family (36)

Family Cites Families (10)

Cited By (1)

Also Published As

Similar Documents